Microsoft's hegemony depends upon two cash cows: Windows and Office. Mark Shuttleworth, the founder of Ubuntu, has his sights firmly set on Windows, and has both the means, the chutzpah, and the community to credibly commandeer an assault on Fortress Redmond, as suggested by Ashlee Vance in The New York Times over the weekend.

Others have tried to beat Microsoft at its own game and have failed miserably. The difference with Shuttleworth, however, is that he's not necessarily trying to beat Microsoft at its game. He's hoping to "fundamentally change the operating system market," something that might wrong-foot Microsoft and give Ubuntu a fighting chance.

There are signs that Ubuntu is already stealing a march on Microsoft, as noted in the article:

Roughly half of Google's 20,000 employees run a version of Ubuntu. With this crowd of early adopters standing behind Ubuntu, a crowd with a massive profit machine behind them, anything can happen;

IDC estimates that 11 percent of American businesses have systems based on Ubuntu, with even broader penetration likely in Europe and elsewhere;

Canonical, the company behind Ubuntu, is approaching $30 million in annual revenue, which may seem like a gnat on Microsoft's bison-esque backside, but this revenue represents multi-million dollar commitments from Dell, IBM, and other large parties with an interest in unshackling themselves from Microsoft. In other words, the nature of the revenue is more telling than the amount;

Ubuntu commands the fealty of tens of thousands of unpaid volunteers globally, despite Canonical only employing 200 or so employees. Ubuntu has leverage well beyond its means.

So, game on. However, the big test for Ubuntu will be whether it's prepared to make some concessions to business reality in order to succeed. I've talked at length with Shuttleworth on this topic and, while I remain convinced that he has his community's best interests at heart, I believe that Ubuntu's community is going to need to mature beyond the "free as in beer and freedom" mentality to also include "free as in market and profit."

Those that think that there is some fundamentally new way to make money with the Web and open source haven't been paying attention. There are certainly new ways to distribute software and associated services, but whether in the cloud or on the desktop, there's always some element of control, and that control may jar the faithful.

The big question is how Ubuntu will make its money as it goes from $30 million to $300 million. If it can find a credible cloud strategy that separates desktop development from revenue development (cloud), Shuttleworth will have managed to accomplish the nearly impossible: making gobs of money without upsetting his community. If anyone can, he can. But don't be foolish enough to believe it's going to be painless.